(Z)-1-Acetoxy-2-(acetoxymethyl)-3-nonene | 133490-86-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-1-Acetoxy-2-(acetoxymethyl)-3-nonene
• 英文别名: [(Z)-2-(acetyloxymethyl)non-3-enyl] acetate
• CAS: 133490-86-5
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: NKWDLLSYZVGSFM-HJWRWDBZSA-N

物化性质

• 沸点：
  329.1±35.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  18.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-Acetoxy-2-(acetoxymethyl)-3-nonene 以 水 、 叔丁醇 为溶剂， 生成 2-[(Z)-hept-1-enyl]propane-1,3-diol 、 Acetic acid (Z)-(S)-2-hydroxymethyl-non-3-enyl ester
  参考文献：
  名称：

  Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks

  摘要：

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

  DOI：

  10.1021/jo00031a039
• 作为产物：
  描述：

  1-Acetoxy-2-(acetoxymethyl)-3-nonyne 在 Lindlar's catalyst 2,6-二甲基吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 以95%的产率得到(Z)-1-Acetoxy-2-(acetoxymethyl)-3-nonene
  参考文献：
  名称：

  Enzymes in organic synthesis: remarkable influence of a π system on the enantioselectivity in PPL catalysed monohydrolysis of 2-substituted 1,3-diacetoxypropanes.

  摘要：

  DOI：

  10.1016/s0957-4166(00)82383-6